
Holiday rentals with outdoor seating in Chesterton
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Quick stats about holiday rentals with outdoor seating in Chesterton

Total holiday rentals
Explore 30 holiday rentals in Chesterton

Nightly prices starting at
Chesterton holiday rentals start at $155 NZD per night before taxes and fees

Verified guest reviews
Over 3,880 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chesterton holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesterton rentals

4.9 Average rating
Chesterton stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated Holiday Houses with Outdoor Seating in Chesterton
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

Cabin on Swede Hill
Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

Lakeside Dome Retreat w Hot Tub Near Indiana Dunes
Welcome to Valparaiso Lakeside Retreat a private getaway on Long Lake featuring a one-of-a-kind outdoor geodesic dome (11 feet), hot tub, fire pit, & kayaks. 20 minutes from Indiana Dunes National Park. Perfect for couples, remote workers & nature lovers seeking a tranquil escape. Enjoy stunning Long Lake views from your private backyard & dome. Long Lake public beach access is just around the corner. Perfect for kayaking, swimming, or a morning walk to the water. Book this unique stay today!

Blue Birdhouse - Indiana Dunes
Welcome to The Birdhouse - Your Perfect Getaway! 🐦🌿 Nestled near the Indiana Dunes National Lakeshore, our cozy 2-bedroom, 1-bathroom home is perfect for families, couples, and nature lovers. Enjoy a pet-friendly, fully fenced yard, free parking for 2 vehicles, a fully equipped kitchen, laundry, and a BBQ grill with patio for outdoor dining. Minutes from Lake Michigan beaches, hiking trails, and local dining, it’s the ideal spot for beachgoers and adventurers. Book your stay today! 🌞🏖️🌳

South Shore Studio Apartment {National Park}
I have to warn you definitely not a hook up spot or party house!!! typically rise with rooster on this 5 acre country setting with a small fishing pond. 420 friendly .. Quiet hours are 11 -8 generally some music playing, musicians are welcome !! if you happen to book on a Sunday i host an Open Mic in my Barn every Sunday ..... pretty relaxed. Upon arriving, turn into the driveway, and then right into the yard. Apartment is upstairs, the door is open with the keys inside. ✌️

Lake Trail Cottage
Located just 1 mile from Lake Michigan. Lake Trail Cottage is the closest home in Pines and just minutes from Beverly Shores beaches! The cottage has two bedrooms one bath. With basement Rec room. Home sleeps 7. The primary bedroom features a Queen bed, 42in Smart TV. The second room has a full size bed. Pullout couch/ living room. Calumet Trail and South Shore Train (Chicago)is located directly behind home. South Shore train to Chicago is 1 mile from house. Bikes & beach supplies included.

Dunes Vacation Rental
Near beach, casino, dunes and an easy drive to Chicago, Michigan and Notre Dame! Walkable to South Shore Train (Chicago). Features: Signature deck with gas grill, hot tub, outdoor shower, dining table, lounge area and fire pit. Luxury lower level with its own living area, tv, two bedrooms, three bathrooms, a bar and laundry. Upstairs features an open kitchen/dining room with gas fireplace, separate living room, full bathroom with dual shower heads, a master suite and two bunkbed rooms.

Bro’s Place 6 mile drive to Indiana Dune’s
Welcome if you like country life Bro’s place is the place to be...watching the sheep, chickens and wildlife on you back deck making dinner on the grill with a full kitchen. Pick your own veggies outside the back door when in season. You will find a welcome basket with snacks, wine and homemade soap in bathroom fresh eggs from our chickens when available if your planning to visit our Beautiful Indiana Dunes you’ll find everything you need..chairs, towels, cooler Queen size sofa sleeper

"myhathouse" detached studio downtown Chesterton
Vaulted skylights allow natural light. Ksize bed. Couch opens into a full size bed. (DEEP cleaned to AirBnb COVID-19 disinfectant standards) Fully stocked kitchen, sm. bathroom w/ shower. Parking ft. of house, 1.5 M from Lake Michigan Shoreline, 2 blocks to 15th St. entry to Prairie-Dune Trail. European Market (May -Oct) each Saturday downtown. Fall season drives along U.S. HW 12 & 20 for foliage Winter day hikes, x-county skis trail, shopping trips to the Michigan City Outlet mall.

New Dunes Escape
Your family will be close to everything when you stay at this centrally-located place. Located just 3 minutes from the entrance of the Indiana Dunes National Park, 45 minutes from Chicago, 45 minutes from New Buffalo, MI , and 3 minutes from the Dunes Park South Shore Station, this completely remodeled home is the perfect place for a get-away. With free wifi, firepit with firewood, and a 4-seasons room, this house is the perfect place to relax after a great day swimming or hiking.

Hot tub open year round in modern/rustic cottage!
Kick back and relax in this rustic & stylish cottage that is surrounded by gorgeous landscaping on almost 2 acres in Harbert. Cherry Beach a 5 min drive, 15 mins to New Buffalo, & minutes to Greenbush, Infusco, Susan's & the new Out There wine bar! Perfect place if you seek peace & quiet - play a record, hit the hot tub, read a book in screened in porch or hammock, hang out by the firepit or jump on one of the 4 bikes! So close to boutiques, coffee shops and cute restaurants!

The Dune Den! Huge Yard/Firepit/Near Town+Dunes
Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this centrally-located home. Things to look forward to: Less than 10 minutes to the Dunes and beaches or head 3 minutes the other way to downtown for food, drinks and plenty of small town fun. This charismatic home greets you with all new furniture, front porch, HUGE fenced yard, and local decor. You will fall in love with this family town so bring the kids!

Miller Mermaid Suite-100 yds from the beach!
100 yds from the beach, the cozy MERMAID BASEMENT SUITE is best for a young family or 2-3 adult friends. This 400 sq ft artsy basement/studio includes: private entrance, kitchenette, unique art, cozy reading/sleeping nook. There is one small window with no lake view but you can see the lake from the upstairs deck. BBQ on the grill. Visit local restaurants, shops & galleries. Hike wooded trails & swim by sandy, dune-grass beaches. . House-trained dogs welcome!
Popular amenities for Chesterton outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Steps to Beach & Starbucks! Private Yard, Firepit!

Dune National Park - Nature Lover's Retreat

The Lake Escape - 5 Mins from beach, casino, & zoo

The Ashlin House.

Quiet Nature Escape in New Buffalo

Pet Friendly, Fenced Yard, and Hot Tub Getaway

Newly Renovated with Finished Basement

Beach! Hot Tub! New Buffalo! Firepit! King Bed!
Apartment rentals with outdoor seating

1Plant MOOD FREE Wi-Fi Street Parking Washer/Dryer

Cute Skylar: Valparaiso University ShortTerms

Beachcomber Suite - Beaches, Dunes, Golf, Wine Tr

Cozy Chalet by Lake MI&Dunes with Fire Pit

ValpoVilla: Location, location, location!

Morton's Retreat Cozy 1 Bedroom Apartment

Historic Studebaker Carriage House- Lower Level

Second Floor Apartment sitting on Pine Lake
Condo rentals with outdoor seating

Lakeside Serenity: One-Bedroom Villa

South Shore Dr Retreat

Updated Cottage Downtown, walk to Beach

MTM Premier Properties-on acres of tranquility

Perfect Location Condo Pools Walk to all Beach 1.5

The Broadway Special - 2 Bd/1 Bath Smart-Condo!

Nightingale Dunes - Modern beach town retreat

Live the marina life in New Buffalo!
When is the best time to visit Chesterton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $264 NZD | $247 NZD | $247 NZD | $240 NZD | $309 NZD | $328 NZD | $390 NZD | $345 NZD | $295 NZD | $312 NZD | $262 NZD | $268 NZD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Destinations to explore
- Chicago Holiday rentals
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- Cabin rentals Chesterton
- Rentals with a fire pit Chesterton
- Pet-friendly rentals Chesterton
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- House rentals Chesterton
- Family-friendly rentals Chesterton
- Rentals with a patio Chesterton
- Rentals with beach access Chesterton
- Rentals with outdoor seating Porter County
- Rentals with outdoor seating Indiana
- Rentals with outdoor seating United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Soldier Field
- 875 North Michigan Avenue
- The Field Museum
- Warren Dunes State Park
- Humboldt Park
- Shedd Aquarium
- University of Notre Dame
- Guaranteed Rate Field
- University of Chicago
- Union Park
- Lincoln Park Zoo
- Chicago River Walk
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Washington Park Zoo
- Loyola University Chicago
- Indiana Dunes State Park
- Oak Street Beach





